Acetonitrile → HCID 70105058, compound

HRID 279069Notes

Reaction equation

HRID 279069 reaction equation
[C:1]([C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH:20]3[CH2:22][O:21]3)=[CH:16][C:15]=2[O:23][CH:24]([CH3:26])[CH3:25])[N:9]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2].[CH2:27]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(#N)C>O>[C:1]([C:5]([N:7]1[C:8]([NH2:9])=[CH:13][CH:12]=[CH:11][CH:10]1[C:14]1[CH:19]=[CH:18][C:17]([CH:20]([OH:21])[CH2:22][N:38]2[CH2:39][CH2:40][N:35]([CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:36][CH2:37]2)=[CH:16][C:15]=1[O:23][CH:24]([CH3:25])[CH3:26])=[O:6])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 792141-PhenethylpiperazineHCID 22624307HCID 22624307, compound

Product 1

HCID 70105058HCID 70105058, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a 25 mL round-bottomed flask equipped with condenser and N2 inlet were added 300 mg (0.847 mmol) N-t-butylcarbonyl-6-(2-isopropoxy-4-oxiranylphenyl)-pyridin-2-ylamine, 193 mg (1.017 mmol) N-phenethylpiperazine, 9 mL acetonitrile, and 0.85 mL water. The reaction was heated to 80° C. for 20 hours, cooled, and partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic phase was separated, washed with brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using methanol/methylene chloride/ammonium hydroxide as eluant to afford 283 mg (62%) of an off-white foam.

Workup

  1. customTo a 25 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperaturecooled
  3. custompartitioned between ethyl acetate and aqueous sodium bicarbonate
  4. customThe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-83c775c3b9284919a305c3ca9d31fcd9
Source dataset
uspto-grants-2002_03
Patent number
US06362195B1

Reaction notes

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